1: 98 percent / H2 / 5percent Pd/C / tetrahydrofuran; methanol / 5 h / 760 Torr 2: 1.) aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0 deg C, 0.5 h, 2.) 110 deg C, 0.5 h 3: 1.) NaH / 1.) THF, 2.) THF, 60 deg C, 1 h 4: 45 percent / boron tribromide / CH2Cl2 / 0.75 h / 0 - 20 °C View Scheme

With  hydrogen; palladium on activated charcoal in  tetrahydrofuran; methanol Hydrogenation;   

Multi-step reaction with 2 steps 1: 98 percent / H2 / 5percent Pd/C / tetrahydrofuran; methanol / 5 h / 760 Torr2: 1.) aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0 deg C, 0.5 h, 2.) 110 deg C, 0.5 h  

Multi-step reaction with 3 steps 1: 98 percent / H2 / 5percent Pd/C / tetrahydrofuran; methanol / 5 h / 760 Torr2: 1.) aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0 deg C, 0.5 h, 2.) 110 deg C, 0.5 h3: 1.) NaH / 1.) THF, 2.) THF, 60 deg C, 1 h